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Microscale Synthesis and Spectroscopic Analysis of Flutamide, an Antiandrogen Prostate Cancer Drug

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Ryan G. Stabile and Andrew P. Dicks

Department of Chemistry, University of Toronto, Toronto, Ontario, Canada, M5S 3H6

J. Chem. Educ., 2003, 80 (12), p 1439

DOI: 10.1021/ed080p1439

Publication Date (Web): December 1, 2003

Section:

History, Education, and Documentation

Abstract

The microscale preparation of flutamide, a nonsteroidal antiandrogen prescribed as Eulexin for the treatment of prostate cancer is outlined. The synthesis involves N-acylation of a trisubstituted aromatic compound, 3-trifluoromethyl-4-nitroaniline. The procedure is easily adapted to generate structural analogues of flutamide. A significant feature is the curricular flexibility afforded by this experiment. The fundamental reaction is appropriate within an introductory organic laboratory course, demonstrating amine and acid–halide reactivity. Functional group transformations can be observed by IR spectroscopy. ¹H NMR spectra of reactant and products facilitate a thorough examination of shielding and deshielding effects and aromatic proton coupling. With more advanced students there exists the potential to discuss principles of retrosynthetic analysis, pharmaceutical synthesis, and structure–activity relationships.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Feature):

The Microscale Laboratory

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Drugs / Pharmaceuticals

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